Bareboat Chartering in the Caribbean – Dock, Moor, or Anchor?

Key Questions Answered:

• Where can you anchor or moor on a Caribbean charter?
• Do you need to reserve moorings in the BVI?
• What’s the difference between anchoring, mooring, and dockage?
• How do bareboat charterers plan overnight stops?

One of the biggest advantages of a Caribbean yacht charter is the ability to change scenery every night. From marinas and mooring fields to quiet anchorages, each option comes with its own strategy, availability, and level of planning—especially in high-demand destinations like the British Virgin Islands.

A standout experience of chartering a boat for a week in the Caribbean is the ability to spend each night somewhere new—whether tied up at a bustling dock, relaxing on a mooring, or anchored in a serene, secluded bay. 

When Michael Cosgrove and his family bareboat chartered a 42-foot catamaran in July for a week sailing in the British Virgin Islands, they enjoyed all three. “The BVI is a fantastic place to charter with great anchorages and small bars and restaurants at every spot with a short sail in between,” says Cosgrove, who cruised with his wife and three children, ages 10, 12, and 14. “We did anchor a few times during the day for snorkeling stops, but always spent the night on a mooring ball. One night we spent at the dock on Virgin Gorda, which was great. We ended up with that just because of the cancellation.”

If you’re on a crewed yacht charter, it’s the crew who take care of making the overnighting arrangements. If you’re bareboating, it’s up to you. This is especially important since some companies don’t permit night sailing on a bareboat charter. Here’s what to know and how to be prepared:

BEFORE CHARTER BRIEFINGS

Clients bareboating with Dream Yacht, in Annapolis, MD, with Caribbean bases in Antigua, the British Virgin Islands, Grenada, Guadeloupe, Martinique, St. Martin, and the U.S. Virgin Islands, are sent a detailed base guide before departure. Then, clients receive a briefing on board their yacht an hour or so before setting sail. This orientation includes mooring, anchorage, and itinerary help.

Similarly, bareboat charter companies such as The Moorings & Sunsail, in Clearwater, FL, with bases on the Caribbean islands of Antigua, the British Virgin Islands, Grenada, St. Lucia, and St. Martin, provide detailed charts and safety briefings to each guest before they set sail.

“These detail the appropriate anchorages to plan for an itinerary, including mooring balls and anchoring-only areas, as well as any ‘red zones’ that should be avoided due to various hazards and more dangerous conditions. We also provide sample itineraries on our website for each destination, which can help guests plan ahead of their journey the anchorages which they’d like to include on their individual vacations,” says Ian Pedersen, senior marketing manager.

TRANSIENT DOCKAGE

“Staying on the dock at Virgin Gorda was really fun and I’d recommend reserving a slip in advance,” says Cosgrove. 

Many Caribbean marinas offer transient slips. Popular examples include Safe Harbor Puerto Del Rey, Puerto Rico; Scrub Island Resort, Spa & Marina, BVI; Marigot Bay Yacht Haven, St. Lucia; and Clarkes Court Boatyard & Marina, Grenada. However, it is essential to contact marinas directly to confirm availability, as space can be limited and demand varies by season and location. Or, options to reserve online include Dockwa (dockwa.com), which has 8 Caribbean locations on its website, and Snag-a-Slip (www.snagaslip.com) with 4.

“There are also a few marinas in the BVI that offer dockage and Mooring Balls like the Bitter End Yacht Club, Saba Rock, and Scrub Island,” says Raul Bermudez, vice president of MarineMax Vacations, with its base at the Nanny Cay Marina, in Tortola, BVI.

In the Southern Caribbean, marina spaces are few and far between, according to Lesley Dowden, reservationist at Horizon Yacht Charters, at the Blue Lagoon Marina & Hotel, in St. Vincent & the Grenadines. “Sandy Lane in Canouan is the main marina, and there are always plenty of berths available. It is quite pricey, but it is lovely, and charter guests do feel it is worth the expense.” 

OVERNIGHT MOORINGS

Mooring balls are usually plentiful and readily available in most Caribbean charter destinations, says The Moorings & Sunsail’s Pedersen. “These are mostly utilized on a first-come, first-serve basis and paid nightly. However, in a few locations, such as the BVI, there are apps like BoatyBall, through which you can reserve a mooring ball in advance. This is done the morning of and is a bit of a race to reserve one when the reservation window opens before they are all sold out.”

The Tobago Cays have both anchoring and moorings, and the rate is the same for both, so the moorings get taken quickly, says Horizon’s Dowden. “Mustique has limited moorings. You have to pay for 3 nights even if you only want to stay for 1, so booking ahead is advised during prime dates such as Christmas and New Year.”

ANCHORAGES

Anchoring in the Caribbean is generally very good, with many anchorages offering calm, protected conditions and sandy bottoms that provide a secure hold for the anchor. Bareboat companies often give suggestions on where to anchor, and where not to, in their itineraries. For example, a sample suggested route from The Moorings suggests clients pick up a mooring at Cooper Island, as the main harbor here, Manchioneel Bay, has poor holding ground for anchoring. And in Anegada, anchoring is possible in both the inner and outer harbors, where the holding ground is reportedly good. 

“Most islands allow you to anchor, but space may be limited during prime holiday times. Bequia has a huge, open bay with plenty of space to anchor at any time of year,” says Dowden.

There are no anchoring zones in the Caribbean. Some of these include Leinster Bay on St. John, part of the Virgin Islands National Park; Grande Anse Beach in Grenada, as it’s located within the Grand Anse Marine Protected Area; and areas in the Tobago Cays Marine Park, to protect coral reefs and seagrass beds. 

A little advance planning and close attention to the guidance from bareboat companies can ensure a safe and scenic anchorage to enjoy spectacular sunsets and sunrises.

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Competition for Mooring Balls in the BVI and What’s New for the 2025-2026 Season

The morning reservation situation proved a little painful for Michael Cosgrove and his family, who bareboat chartered a 42-foot catamaran in July for a week sailing in the British Virgin Islands. “The last time I dealt with this was years ago, when moorings were first-come, first-served. Now, that is only part of the mooring field, and the other parts are reserved on the BoatyBall app. We had some mild difficulty securing a ball at 7 a.m. when they became available, as they quickly popped up as ‘reserved’. However, we did manage to get through the week with a mooring every night.”

BoatyBall is a web-based application in the BVI that allows boaters to reserve mooring balls, pay for selected first-come, first-served moorings, and accomplish other tasks like making dinner reservations. The app currently has around 400 moorings in the program in the Virgin Islands. The majority are based in the BVI, but there are also some in the USVI, which the Virgin Islands Professional Charter Association oversees. The moorings in the BVI are owned by individual businesses. They are maintained by a local company called Moor Seacure, which has been installing and maintaining moorings in the BVI for over 30 years.

BoatyBall offers boaters the option to pay $40 for a first-come, first-served mooring or $55 to reserve one for the same day. Typically, users book early in the morning, spend the day exploring nearby islands, and return in the evening to tie up at their reserved mooring ball.

“The demand has created challenges,” says Ty Atteberry, who, with Bob Wall, co-founded BoatyBall LLC USA, headquartered in Raleigh, NC. “We have considered making moorings available months in advance, but because of the demand, this would create a secondary market for moorings. For example, one of the major charter companies encouraged us to reserve the moorings months in advance so they could book them all and then make them available to their guests. We believe that would be bad for the BVI, so we have stuck with the 7 a.m. day of booking to prevent this from happening.”

Constantly changing plans based on weather and other unforeseen issues has led to the company processing 2000 cancellations with same-day reservations this past season, adds Atteberry. “It is currently free to create an account. This has created a false demand, with many boats having multiple people trying to reserve at once. This season, we averaged over 400 users on the app every morning trying to reserve.”

To address this issue, BoatyBall has instituted a $15 annual membership fee to reserve a mooring. As Atteberry explains, the small fee effectively weeds out bots and non-serious users, thereby eliminating fake accounts and reducing demand pressure due to the lower number of fake accounts. boatyball.com 

What to Do Next

• Review your charter company’s base guide before departure
• Plan overnight stops in advance—especially in peak season
• Use apps like BoatyBall early in the morning if cruising the BVI
• Confirm marina availability ahead of time for dock stays
• Stay flexible—weather and availability can change quickly

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What This Means for Charterers

The Caribbean offers exceptional flexibility for overnighting, but that freedom now comes with increased competition—particularly for moorings in high-traffic areas like the BVI. Systems like BoatyBall have modernized access, but they’ve also introduced a layer of planning and timing that didn’t exist years ago. 

For bareboat crews, the key is preparation. Understanding where anchoring is permitted, where moorings are required, and when reservations are needed can make the difference between a seamless itinerary and a stressful evening search for space.

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